Methylamine → HCID 178484420, compound

HRID 2239998Notes

Reaction equation

HRID 2239998 reaction equation
[C:1]1([S:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH2:20][CH2:21]OS(C4C=CC(C)=CC=4)(=O)=O)[CH:17]=3)[NH:12][N:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1.[CH3:38][NH2:39]>>[C:1]1([S:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH2:20][CH2:21][NH:39][CH3:38])[CH:17]=3)[NH:12][N:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 178427774HCID 178427774, compound

Product 1

HCID 178484420HCID 178484420, compoundYield 19.4%

Procedure

A solution of toluene-4-sulfonic acid 2-(3-benzenesulfonyl-1H-indazol-5-yloxy)-ethyl ester (0.340 g, 0.720 mmol) in 2.0 M methylamine in THF (8 mL, 16 mmol) was stirred at 70° C. in a sealed tube for about 15.5 hours. After cooling somewhat, the reaction mixture was solvent evaporated and partitioned in chloroform and aqueous sodium bicarbonate. The organic phase was then washed with brine, dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography using 10% methanol in chloroform and 1.0% ammonium hydroxide/10% methanol in chloroform. After drying at 57° C. in vacuo for 20 minutes, [2-(3-benzenesulfonyl-1H-indazol-5-yloxy)-ethyl]-methyl-amine as a light yellow semi-solid (0.0461 g, 19.4%) was obtained. This was dissolved in methanol and chloroform, and ethereal hydrochloride was added. The mixture was concentrated and dried in vacuo at 73° C. for 20 hours to yield the hydrochloride as a tan foam (0.0422 g). Mass Spectrum (+EI, [M+H]+) m/z 332. 1HNMR (500 MHz, DMSO-d6): δ14.24 (s, 1H), 8.89 (s, 2H), 7.96-7.99 (m, 2H), 7.53-7.68 (m, 4H), 7.40 (d, 1H, J=2.19 Hz), 7.25 (dd, 1H, J=9.15 Hz and 2.32 Hz), 4.30-4.32 (m, 2H), 3.33-3.35 (m, 2H), 2.60-2.63 ppm (m, 3H).

Workup

  1. temperatureAfter cooling somewhat
  2. customevaporated
  3. custompartitioned in chloroform
  4. washThe organic phase was then washed with brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography
  9. customAfter drying at 57° C. in vacuo for 20 minutes

Sources & evidence

ORD record
ord-c32f2f1a7e984a83a38e53f82197653d
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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